EP0330136B1 - Neue Zirkonium(IV)-Chelate, deren Herstellung und deren Verwendung in Druckfarben - Google Patents
Neue Zirkonium(IV)-Chelate, deren Herstellung und deren Verwendung in Druckfarben Download PDFInfo
- Publication number
- EP0330136B1 EP0330136B1 EP89102974A EP89102974A EP0330136B1 EP 0330136 B1 EP0330136 B1 EP 0330136B1 EP 89102974 A EP89102974 A EP 89102974A EP 89102974 A EP89102974 A EP 89102974A EP 0330136 B1 EP0330136 B1 EP 0330136B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- zirconium
- chelates
- citric acid
- chelate
- printing inks
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000976 ink Substances 0.000 title claims description 15
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 title claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 13
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 claims description 11
- 229910052726 zirconium Inorganic materials 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000013522 chelant Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 150000003755 zirconium compounds Chemical class 0.000 description 4
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- -1 citric acid ester Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920002678 cellulose Chemical class 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- TVCBSVKTTHLKQC-UHFFFAOYSA-M propanoate;zirconium(4+) Chemical compound [Zr+4].CCC([O-])=O TVCBSVKTTHLKQC-UHFFFAOYSA-M 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 241001482107 Alosa sapidissima Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical group [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Definitions
- Esters of hypothetical zirconium (IV) acid also known as tetraalkyl zirconates
- the alkyl groups can be replaced by chelating groups, which e.g. leads to zirconium acetylacetonate.
- acylates such as zirconium propionate, play a technical role.
- zirconium compounds are problem-free: the alkyl zirconates already cross-link the ink in the storage container, zirconium acetylacetonate dissolves only extremely little in the solvents in question, and zirconium propionate can lead to odor problems.
- one to four of the alkoxy groups of a zirconic acid ester can be replaced by the citric acid ester groups mentioned. Accordingly, the ratio of the alkoxy groups bonded to the central Zr atom to the citric acid ester groups can be between 3: 1 and 0: 4.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3805879A DE3805879C1 (enrdf_load_stackoverflow) | 1988-02-25 | 1988-02-25 | |
| DE3805879 | 1988-02-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0330136A2 EP0330136A2 (de) | 1989-08-30 |
| EP0330136A3 EP0330136A3 (en) | 1990-11-22 |
| EP0330136B1 true EP0330136B1 (de) | 1994-06-15 |
Family
ID=6348126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89102974A Expired - Lifetime EP0330136B1 (de) | 1988-02-25 | 1989-02-21 | Neue Zirkonium(IV)-Chelate, deren Herstellung und deren Verwendung in Druckfarben |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5021596A (enrdf_load_stackoverflow) |
| EP (1) | EP0330136B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH01249781A (enrdf_load_stackoverflow) |
| CA (1) | CA1326857C (enrdf_load_stackoverflow) |
| DE (2) | DE3805879C1 (enrdf_load_stackoverflow) |
| ES (1) | ES2056977T3 (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4115034A1 (de) * | 1991-05-08 | 1992-11-12 | Bayer Ag | Verfahren zur herstellung von metallcarboxylaten sowie deren verwendung fuer die polymerisation von fuer eine ziegler-natta-polymerisation geeigneten monomeren |
| DE4242622A1 (de) * | 1992-12-17 | 1994-06-23 | Bayer Ag | Neue Titan(IV)-chelate und ihre Verwendung in Polysiloxanmassen |
| GB9412579D0 (en) * | 1994-06-22 | 1994-08-10 | Tioxide Specialties Ltd | Compositions containing zirconium compounds |
| GB2290545B (en) * | 1994-06-22 | 1998-03-11 | Tioxide Specialties Ltd | Printing inks containing zirconium compounds |
| US5897694A (en) * | 1997-01-06 | 1999-04-27 | Formulabs | Methods for improving the adhesion and/or colorfastness of ink jet inks with respect to substrates applied thereto, and compositions useful therefor |
| USH1967H1 (en) * | 1998-07-02 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Methods for improving the adhesion and/or colorfastness of ink jet inks with respect to substrates applied thereto |
| US20030091647A1 (en) * | 2001-11-15 | 2003-05-15 | Lewis Jennifer A. | Controlled dispersion of colloidal suspensions via nanoparticle additions |
| US20040226620A1 (en) * | 2002-09-26 | 2004-11-18 | Daniel Therriault | Microcapillary networks |
| US7141617B2 (en) * | 2003-06-17 | 2006-11-28 | The Board Of Trustees Of The University Of Illinois | Directed assembly of three-dimensional structures with micron-scale features |
| US7956102B2 (en) * | 2007-04-09 | 2011-06-07 | The Board Of Trustees Of The University Of Illinois | Sol-gel inks |
| US7922939B2 (en) * | 2008-10-03 | 2011-04-12 | The Board Of Trustees Of The University Of Illinois | Metal nanoparticle inks |
| US8187500B2 (en) * | 2008-10-17 | 2012-05-29 | The Board Of Trustees Of The University Of Illinois | Biphasic inks |
| US10259953B2 (en) * | 2016-09-30 | 2019-04-16 | Borica Co., Ltd. | Adhesion promoted and ink composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB885679A (en) * | 1956-12-21 | 1961-12-28 | Union Carbide Corp | Organic zirconium derivatives and paint, oil and organic-base ink compositions containing them |
| US4065544A (en) * | 1970-05-11 | 1977-12-27 | Union Carbide Corporation | Finely divided metal oxides and sintered objects therefrom |
| US3682688A (en) * | 1970-06-17 | 1972-08-08 | Du Pont | Method of fixing a chelated organic titanate vehicle to a substrate |
| US4160051A (en) * | 1972-03-17 | 1979-07-03 | I.W.S. Nominee Company Limited | Zirconium flame-resist treatment |
| US4623738A (en) * | 1985-04-22 | 1986-11-18 | Kenrich Petrochemicals, Inc. | Neoalkoxy organo-titanates and organo-zirconates useful as coupling and polymer processing agents |
| DE3733608A1 (de) * | 1987-10-05 | 1989-04-13 | Huels Troisdorf | Neue titan(iv)-chelate und ihre verwendung in druckfarben |
-
1988
- 1988-02-25 DE DE3805879A patent/DE3805879C1/de not_active Expired
-
1989
- 1989-02-21 JP JP1039485A patent/JPH01249781A/ja active Pending
- 1989-02-21 CA CA000591628A patent/CA1326857C/en not_active Expired - Fee Related
- 1989-02-21 ES ES89102974T patent/ES2056977T3/es not_active Expired - Lifetime
- 1989-02-21 DE DE58907862T patent/DE58907862D1/de not_active Expired - Fee Related
- 1989-02-21 EP EP89102974A patent/EP0330136B1/de not_active Expired - Lifetime
- 1989-02-23 US US07/314,816 patent/US5021596A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01249781A (ja) | 1989-10-05 |
| EP0330136A3 (en) | 1990-11-22 |
| US5021596A (en) | 1991-06-04 |
| DE3805879C1 (enrdf_load_stackoverflow) | 1989-08-10 |
| EP0330136A2 (de) | 1989-08-30 |
| DE58907862D1 (de) | 1994-07-21 |
| CA1326857C (en) | 1994-02-08 |
| ES2056977T3 (es) | 1994-10-16 |
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